Triethylamine → HCID 68108868, compound

HRID 2179422Notes

Reaction equation

HRID 2179422 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[O:14][C:15]3[C:20]([Cl:21])=[CH:19][C:18]([S:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)(=[O:24])=[O:23])=[CH:17][C:16]=3[C:10]=2[CH:9]1[C:31]([OH:33])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:34]([N:36](CC)[CH2:37]C)C.Cl.CNC.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>C(#N)C>[Cl:21][C:20]1[C:15]2[O:14][C:11]3[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7])[CH:9]([C:31](=[O:33])[N:36]([CH3:37])[CH3:34])[C:10]=3[C:16]=2[CH:17]=[C:18]([S:22]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)(=[O:24])=[O:23])[CH:19]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 68109219HCID 68109219, compound

Product 1

HCID 68108868HCID 68108868, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of the product obtained from step A (80 mg, 0.16 mmol) in anhydrous acetonitrile (1.5 mL) was added triethylamine (45 μL, 0.32 mmol) followed by dimethylamine hydrochloride (20 mg, 0.24 mmol) and benzotriazole-1-yl-oxy-tris-(dimethylamino)-phosphoniumhexafluorophosphate (106 mg, 0.24 mmol). After stirring at ambient temperature for 12 h, the resulting solution was concentrated to dryness in vacuo. The reaction mixture was diluted with ethyl acetate (20 mL), washed sequentially with saturated aqueous NaHCO3 (10 mL) and brine (10 mL), and dried over anhydrous MgSO4. After filtration, the filtrate was concentrated in vacuo to give the crude product which was purified by flash column chromatography (SiO2, 9:1 to 3:2 hexanes/ethyl acetate) to afford tert-butyl 6-chloro-1-(dimethylcarbamoyl)-8-(phenylsulfonyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (60 mg, 71%) as a colorless oil: 1H NMR (CDCl3, 400 MHz) δ 7.93-7.77 (m, 4H), 7.57-7.48 (m, 3H), 6.19 (s, 1H), 4.53-4.27 (m, 1H), 3.76-3.62 (m, 2H), 3.43 (s, 3H), 3.02 (s, 3H), 2.85-2.80 (m, 1H), 1.49 (s, 9H).

Workup

  1. concentrationthe resulting solution was concentrated to dryness in vacuo
  2. additionThe reaction mixture was diluted with ethyl acetate (20 mL)
  3. washwashed sequentially with saturated aqueous NaHCO3 (10 mL) and brine (10 mL)
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated in vacuo
  7. customto give the crude product which
  8. customwas purified by flash column chromatography (SiO2, 9:1 to 3:2 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-42897979c2f143edb2e56a24dcca11c9
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

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